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Study on Domino Reaction of 2-(2-Alkynylarylidene)-1,3-Dicarbonyl Compounds

Author: LiuLu
Tutor: ZhangJunLiang;LuYong
School: East China Normal University
Course: Physical and chemical
Keywords: Acid-catalyzed Tandem reaction Cyclization reaction Polycyclic compounds Selective Synthesis
CLC: O621.2
Type: PhD thesis
Year: 2010
Downloads: 74
Quote: 0
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Benzo polycyclic compounds are widely present in many natural products, has been widely used in many fields of medicine, agriculture, food industry, functional materials, printing and dyeing. In synthetic chemistry, but also the synthesis of complex natural products or non-natural product, the key intermediates. Therefore, based on the chemical study of the synthesis of polycyclic compounds and its transformation has been one of the hot spots of organic chemistry research. Starting from the same substrate by changing the reaction conditions, or by modification of the structure of the substrate to achieve a selective synthesis of different structures of the product, is a very significant and very challenging research topics. O alkynyl benzaldehyde and 1,3 - dicarbonyl compounds as raw materials, through the condensation reaction Synthesis of 2 - (2 - alkynyl aryl ylidene) - 1,3-dicarbonyl compounds. We found that these compounds for the substrate reaction, can achieve selective synthesis of a series of different benzo by changing the reaction conditions or a change in the alkynyl group, and a ketone carbonyl group substituent, a polycyclic compound. We first studied the 2 - (2 - alkynyl aryl ylidene) nsted acid and a Lewis acid, 1,3 - dicarbonyl compounds in the presence of an acid (Br (?)) Catalyzed benzo cyclization reaction. When the the ketocarbonyl next substituent is alkyl, can be obtained in which under acid catalyzed substituted naphthyl; substituents beside the ketone carbonyl group is a phenyl group, we found that under the different reaction conditions can be selectively the multi-substituted naphthalene or benzo [a] lumefantrine; the alkynyl end connection is alkyl, you can also get multi-substituted naphthalene acetylene. Research in the mechanism, we study the asymmetric 1,3 - dione compound of the mechanism of a preliminary understanding. Next, we found that: the connection when the end of the alkynyl group of 2 - (2 - alkynyl aryl ylidene) - 1,3-dicarbonyl compound is cyclopropane, two rearrangement reaction occurs in the Lewis acid catalyzed. When AgSbF6 as a catalyst, mainly generated naphthyl ketone compound; When using In (OTf) 3 as catalyst, while methanol as additives, mainly obtained naphthyl cyclopropyl formaldehyde. Meanwhile, the migration ability of the migrating Group also has a great influence on the selectivity of the reaction. We also carried out a preliminary study of the reaction mechanism. Finally, we replace beside the ketone carbonyl group of the 2 - (2 - alkynyl aryl ylidene) -1,3 - dicarbonyl compound with electron rich aromatics, and can occur when a series Nazarov cyclization-Conia-ene reaction obtained double carbocyclic compound (which can generate a 5,5 -, 5,6 - and 5,7 - double ring compounds). The good news is that further research found that o-alkynyl benzaldehyde and 1,3 - dicarbonyl compounds as raw materials, through the one-pot, multi-step tandem reaction, you can quickly get double carbon ring compounds. Interestingly, we found that: in the Knoevenagel condensation reaction of the catalyst used in pyridine acetate conducive to promoting the next reaction, and can effectively improve the yield of the system a series Nazarov cyclization and Conia-ene reaction, and therefore A series of catalysts.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds
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